Summer in Westport is unbeatable, but if you’ve never been sailing here, you’re missing out: we have multiple waterways to traverse with the Longshore waterfront, the Saugatuck River, and the Long Island Sound. Westport Lifestyle spoke to Jane Pimental of Longshore Sailing School to get her tips on trying your hand at sailing this summer. What are you waiting for?
Westport Lifestyle: What is the first (or most important) thing newbies should know about sailing?
JP: Understanding wind direction is fundamental to sailing. It determines your course, sail trim, and how the boat handles in different conditions. A good sailor knows how to anticipate shifts, maintain balance, and execute maneuvers with precision—all by watching the wind.
WL: What gear/clothing/equipment do you recommend new sailors get before they hit the water?
JP: Sailing with Longshore Sailing School is all about showing up—no fancy gear required. We provide boats and life jackets (for adults), so there’s no need to invest in equipment. Just come dressed to move: wear closed-toe shoes that can get wet and bring layers to stay comfortable as the weather shifts. The conditions may change, but you’ll be ready.
WL: What surprises newcomers to sailing most?
JP: It’s easy to think sailing is just about getting out and back, but becoming a truly capable sailor takes observation, instinct, and practice.
Learning to read the water—and the subtle signs of changing wind—is one of those unexpected skills that separates beginners from sailors. And it’s often what surprises people the most.
WL: What are some reasons you think people should try sailing if they never have?
JP: Sailing offers something rare: the perfect balance of adventure, independence, and calm. It’s a chance to step away from screens and schedules, and into the rhythm of wind and water.
You’re not just a passenger—you’re in control of your own vessel, learning new skills that challenge your body and engage your mind. Along the way, you’ll meet others who share the same spirit of curiosity and discovery.
Whether you’re chasing the thrill of harnessing the wind or seeking the quiet, sailing opens up a world that’s both energizing and deeply peaceful.
WL: What do you love most about sailing in Westport?
JP: Sailing in Westport is a blend of ease, beauty, and choice. From the Longshore waterfront, it’s a quick glide to the Saugatuck River mouth, the scenic Norwalk Islands, or the wide expanse of Long Island Sound. Whether you prefer the calm of sheltered waters or the excitement of open wind and waves, there’s a course for every kind of sailor.
Though sailing is often seen as an exclusive sport, Westport tells a different story. With both public programs and membership-based clubs, access is broad and welcoming. Whether you’re just getting your sea legs or already charting your own course, there’s a place for you here.
For more info, visit longshoresailing.com